US7504043B2 - Hydrofluorocarbon-based composition and use thereof - Google Patents
Hydrofluorocarbon-based composition and use thereof Download PDFInfo
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- US7504043B2 US7504043B2 US10/570,938 US57093804A US7504043B2 US 7504043 B2 US7504043 B2 US 7504043B2 US 57093804 A US57093804 A US 57093804A US 7504043 B2 US7504043 B2 US 7504043B2
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- heat transfer
- refrigerant
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- 239000000203 mixture Substances 0.000 title claims abstract description 39
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 32
- 239000003507 refrigerant Substances 0.000 claims description 19
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 17
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 16
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 claims description 16
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000003380 propellant Substances 0.000 claims description 9
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 8
- 239000012487 rinsing solution Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 4
- 239000001273 butane Substances 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 2
- 229960003750 ethyl chloride Drugs 0.000 claims description 2
- 239000001282 iso-butane Substances 0.000 claims description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- KFUSEUYYWQURPO-OWOJBTEDSA-N trans-1,2-dichloroethene Chemical group Cl\C=C\Cl KFUSEUYYWQURPO-OWOJBTEDSA-N 0.000 claims description 2
- 238000004378 air conditioning Methods 0.000 abstract description 7
- 238000005057 refrigeration Methods 0.000 abstract description 7
- 239000003921 oil Substances 0.000 description 51
- 150000004996 alkyl benzenes Chemical class 0.000 description 12
- 239000002480 mineral oil Substances 0.000 description 12
- 239000000314 lubricant Substances 0.000 description 10
- 235000010446 mineral oil Nutrition 0.000 description 10
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229920001515 polyalkylene glycol Polymers 0.000 description 6
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 3
- -1 PolyOl Ester Chemical class 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000004781 supercooling Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
- C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25B—REFRIGERATION MACHINES, PLANTS OR SYSTEMS; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS
- F25B2400/00—General features or devices for refrigeration machines, plants or systems, combined heating and refrigeration systems or heat-pump systems, i.e. not limited to a particular subgroup of F25B
- F25B2400/18—Refrigerant conversion
Definitions
- a subject matter of the present invention is a composition based on HFCs (HydroFluoroCarbons), its use in refrigeration and/or air conditioning, and a heat transfer system comprising it.
- Heat transfer systems include in particular refrigerators, heat pumps and conditioned air systems.
- a refrigerant with a suitable boiling point is evaporated at low pressure, taking heat from a first surrounding medium (or zone).
- the vapor thus formed is then compressed by means of a compressor and subsequently passes into a condenser, in which it is converted to the liquid state, giving rise to a release of heat into a second surrounding zone.
- the liquid thus condensed subsequently moves through a pressure-reducing valve, at the outlet of which it is converted to a two-phase mixture of liquid and vapor, which is finally introduced into the evaporator, where the liquid is again evaporated at low pressure, which completes the cycle.
- the mechanical energy required to ensure the compression of the vapor and the circulation of the fluid is provided by an electric motor or an internal combustion engine. As in any mechanical device, it is necessary for the moving parts to be suitably lubricated.
- the lubricants used form an integral part of the heat transfer system and condition both its performance and its lifetime by the maintenance over time of suitable lubrication.
- the refrigerant which is at each pass through the compressor in contact with the lubricant present on its moving parts, tends to carry away a certain amount thereof, which accompanies the refrigerant in its cycle and is thus found in the evaporator.
- the latter is generally brought to a low temperature, at which the viscosity of the lubricant is particularly high, so that there is a risk of lubricant accumulating in the evaporator and thus the lubricant is no longer able to return to the compressor, this return being described in the present text as “oil return”.
- R-22 or monochlorodifluoromethane is a refrigerant of HCFC (HydroChloroFluoroCarbon) type widely used in heat transfer applications, including fixed air conditioning, commercial and industrial refrigeration, and heat pumps.
- HCFC HydrochloroFluoroCarbon
- R-22 has a very low ozone depletion potential (hereinafter ODP)
- ODP ozone depletion potential
- R-407C has in particular been developed for replacing R-22 in air conditioning applications.
- This product is a mixture combining R-32, R-125 and R-134a in the proportions of 23/25/52% by weight.
- R-32 is the usual name in the trade for difluoromethane
- R-125 is pentafluoroethane
- R-134a denotes 1,1,1,2-tetrafluoroethane.
- R-407C has thermodynamic properties which are very similar to those of R-22.
- thermodynamic properties concerned are well known to a person skilled in the art and are in particular the refrigerating capacity, the coefficient of performance (or COP) and the condensation pressure.
- the refrigerating capacity represents the refrigeration power available by virtue of the refrigerant, for a given compressor.
- R-22 In order to replace R-22, it is essential to have available a fluid having a high refrigerating capacity close to that of R-22.
- the COP expresses the ratio of the refrigerating energy delivered to the energy applied to the compressor in order to compress the refrigerant in the vapor state.
- a COP value of the refrigerant which is less than that of R-22 is suitable, if an increase in the consumption of electricity of the plant is accepted.
- condensation pressure indicates the stress exerted by the refrigerant on the corresponding mechanical parts of the refrigerating circuit.
- a refrigerant capable of replacing R-22 in a refrigeration system designed for the latter must not exhibit a condensation pressure significantly greater than that of R-22.
- novel HFC-based products in particular R-407C, are not, however, compatible with the mineral oils or alkylbenzene oils used for systems operating with R-22 as regards the lubrication of mechanical parts, in particular because of an inadequate oil return. They thus require the use of novel oils of PolyOl Ester (POE) or PolyAlkylene Glycol (PAG) type.
- POE PolyOl Ester
- PAG PolyAlkylene Glycol
- JP 8-100170 discloses a quaternary composition comprising difluoromethane, trifluoroethane, tetrafluoroethane and pentafluoroethane as replacement for R-502.
- FIG. 1 is a schematic of a refrigeration circuit suitable for measuring oil return.
- a subject matter of the present invention is a composition composed essentially of 15 to 35% by weight of R-32, of 10 to 50% by weight of R-125, of 30 to 50% by weight of R-134a and of 5 to 20% by weight of R-143a.
- a composition composed essentially of 15 to 30% by weight of R-32, of 20 to 40% by weight of R-125, of 35 to 50% by weight of R-134a and of 5 to 15% by weight of R-143a is preferred.
- R-143a denotes 1,1,1-trifluoroethane.
- This composition can be substituted for R-22 in its various applications, in particular for air conditioning. It advantageously exhibits a thermodynamic performance which allows it to be substituted without disadvantage for R-22 in a heat transfer plant designed to operate with this refrigerant, making possible in particular a satisfactory oil return despite the presence of a residual amount of old mineral oil or alkylbenzene oil in the new oil of POE type after the rinsing (or cleaning) operation. Thus, the rinsing operation can be simplified.
- composition according to the invention can thus be used as refrigerant in a heat transfer system suitable for R-22 and comprising a POE or PAG oil as lubricant.
- the lubricant can comprise residual amounts of mineral oil or alkylbenzene oil resulting from the rinsing operation. Another subject matter of the present invention is this use.
- composition which is a subject matter of the present invention can be prepared by methods well known to a person skilled in the art, such as by mixing each of its components in the liquid state in the desired proportions.
- a subject matter of the present invention is a heat transfer system suitable for R-22 and comprising, as refrigerant, the composition as defined above.
- the lubricant employed in such a system is advantageously an oil of polyol ester type or polyalkylene glycol type.
- the heat transfer systems are refrigeration systems, air conditioning systems or heat pumps. Air conditioning systems are particularly preferred.
- a rinsing solution comprising one or more propellant(s) A of nonflammable HFC type, advantageously chosen from R-134a, R-125 and R-227a (1,1,1,2,3,3,3-heptafluoropropane), and one or more compound(s) B, chosen from propane, butane, isobutane, propylene, trans-1,2-dichloroethylene, ethyl chloride, dimethyl ether or methoxymethane and carbon dioxide, is used to remove the old lubricating oil.
- propellant(s) A of nonflammable HFC type advantageously chosen from R-134a, R-125 and R-227a (1,1,1,2,3,3,3-heptafluoropropane
- compound(s) B chosen from propane, butane, isobutane, propylene, trans-1,2-dichloroethylene, ethyl chloride, dimethyl ether or methoxymethane and carbon dioxide
- the rinsing solution preferably comprises from 80 to 99% by weight of propellant(s) A and from 1 to 20% by weight of compound(s) B.
- it comprises from 90 to 99% by weight of A and from 1 to 10% by weight of B.
- the rinsing solution which is advantageously preferred comprises from 12 to 94% by weight of propellant(s) A, from 0.15% to 19% by weight of compound(s) B and from 5 to 85% by weight of POE or PAG oil.
- the rinsing solution which is even more preferred comprises from 54 to 79% by weight of propellant(s) A, from 0.6 to 8% by weight of compound(s) B and from 20 to 40% by weight of POE or PAG oil.
- compositions according to the present invention were prepared and subjected to the following tests.
- a charge of 10 g of a mixture of mineral oil (M) or alkylbenzene oil (AB) with a polyol ester (POE) oil is introduced into a refrigerated coil ( 1 ) placed in a cryostat ( 2 ) at 0° C.
- This coil is connected upstream, via a pipe fitted with a shut-off valve ( 3 ) and a pressure sensor ( 4 ) , to a cylinder ( 5 ) containing the composition according to the invention to be tested, equipped with a dip pipe and placed in a bath at 30° C.
- the coil is extended downstream via a pipe fitted with a regulating valve ( 6 ) and with a shut-off valve ( 7 ) which arrives in the bottom part of a collecting cylinder ( 8 ) placed in a heat bath at 60° C.
- a pipe exiting from the top part of the collecting cylinder is fitted with a gas meter ( 9 ).
- the circuit described in FIG. 1 is representative of a refrigerating circuit in the vicinity of the evaporator and the oil return test consists in measuring the fraction of the oil charge placed in the coil which is carried away by the refrigerant.
- a stream of the composition according to the invention to be tested is circulated for 15 minutes, by initial opening of the shut-off valve ( 7 ) and then of the shut-off valve ( 3 ), through the circuit described above and in particular through the coil containing the oil charge at a flow rate of approximately 1 m 3 /h, measured at ambient temperature and under 1 atmosphere.
- the amount of oil recovered in the cylinder ( 8 ) is weighed.
- the degree of recovery or “oil return” (expressed as a percentage) is equal to the weight of the oil thus recovered divided by the weight of the oil charge placed initially in the coil.
- the maximum allowable level of mineral oil or alkylbenzene oil in a POE oil is defined as being that beyond which the oil return of the mixture is less than that of R-22 under the same conditions of the test.
- composition according to the invention was evaluated on a refrigerating loop, the operating conditions of which are: an evaporation temperature of 0° C., a compressor intake temperature of 15° C., a condensation temperature of 40° C. and supercooling of the liquid at the condenser outlet of 5 K.
- R-32, R-125, R-134a and R-143a of the various compositions prepared and their thermodynamic performances are collated in table 1.
- R-22 and R-407C are also shown.
- the oil return of R-407C, of the various compositions prepared and of R-22 for various mixtures of POE oil with an alkylbenzene oil (table 2) or a mineral oil (table 3) have been listed. It is possible, by extrapolation to an oil return equivalent to that in the presence of R-22, to obtain the maximum allowable level of alkylbenzene oil or mineral oil in the POE for the oil return not to be less than that in the presence of R-22 (table 4).
- compositions illustrated have a refrigerating capacity which is greater than that of R-407C and withstand higher maximum allowable levels of mineral oil or alkylbenzene oil than R-407C.
- composition according to the invention comprises 15% by weight of R-32, 25% by weight of R-125, 50% by weight of R-134a and 10% by weight of R-143a.
- the refrigerating capacity of such a composition is 3240 kJ/m 3 , the COP is 5.6 and the condensation pressure is 15.5 bar.
- the maximum allowable level of mineral oil is 10.7% and that of the alkylbenzene is 14%.
- the procedure is the same as above but with a composition comprising 20% by weight of R-32, 45% by weight of R-125, 15% by weight of R-134a and 20% by weight of R-143a.
- the refrigerating capacity of such a composition is 3950 kJ/m 3 , the COP is 5.3 and the condensation pressure is 19.7 bar.
- the maximum allowable level of mineral oil is 7.3% and that of the alkylbenzene is 14%.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Fireproofing Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0311025 | 2003-09-19 | ||
FR0311025A FR2860001B1 (fr) | 2003-09-19 | 2003-09-19 | Composition a base d'hfc (hydrofluorocarbures) et son utilisation |
PCT/FR2004/002231 WO2005028586A2 (fr) | 2003-09-19 | 2004-09-02 | Composition a base d'hfc (hydrofluorocarbures) et son utilisation |
Publications (2)
Publication Number | Publication Date |
---|---|
US20070187638A1 US20070187638A1 (en) | 2007-08-16 |
US7504043B2 true US7504043B2 (en) | 2009-03-17 |
Family
ID=34224357
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/570,938 Active 2025-03-28 US7504043B2 (en) | 2003-09-19 | 2004-09-02 | Hydrofluorocarbon-based composition and use thereof |
Country Status (9)
Country | Link |
---|---|
US (1) | US7504043B2 (es) |
EP (2) | EP1664234B1 (es) |
JP (1) | JP4855256B2 (es) |
CN (1) | CN1852963B (es) |
AT (1) | ATE451437T1 (es) |
DE (1) | DE602004024548D1 (es) |
ES (1) | ES2336795T3 (es) |
FR (1) | FR2860001B1 (es) |
WO (1) | WO2005028586A2 (es) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10035939B2 (en) * | 2016-09-27 | 2018-07-31 | Icool Ningbo Co.,Ltd | Refrigerant composition and its preparation method |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
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CN100460479C (zh) * | 2006-07-10 | 2009-02-11 | 浙江蓝天环保高科技股份有限公司 | 一种环保型热泵混合工质 |
GB2447629A (en) * | 2007-03-19 | 2008-09-24 | Rpl Holdings Ltd | Refrigerant composition comprising three hydrofluorocarbon components |
US8703690B2 (en) | 2008-03-07 | 2014-04-22 | Arkema Inc. | Use of R-1233 in liquid chillers |
BRPI0906343A2 (pt) * | 2008-04-15 | 2017-05-23 | Du Pont | composições de pentafluoretano, tetraflueoretano e n-butano. |
CN103865491A (zh) * | 2009-05-08 | 2014-06-18 | 霍尼韦尔国际公司 | 用于热泵热水器的氢氟烃制冷剂组合物 |
WO2011066833A1 (en) | 2009-12-01 | 2011-06-09 | Agramkow Fluid Systems A/S | A method and equipment for servicing cooling systems in vehicles |
FR2986309B1 (fr) * | 2012-01-26 | 2018-05-25 | Arkema France | Systeme de refrigeration en cascade |
TW201412966A (zh) * | 2012-08-30 | 2014-04-01 | Du Pont | 為二氟氯甲烷設計之設備的再充填方法 |
FR3013811B1 (fr) | 2013-11-22 | 2019-06-07 | Dynaes | Pompe a chaleur. |
CN107513373A (zh) * | 2017-02-22 | 2017-12-26 | 唐建 | 一种应用于空调/热泵系统中的环保制冷剂 |
WO2019112060A1 (ja) * | 2017-12-07 | 2019-06-13 | ダイキン工業株式会社 | R32、R125、R143a及びR134aを含む冷媒を含有する組成物、並びに、その組成物を用いた冷凍方法、冷凍機の運転方法及び冷凍機 |
JP6729626B2 (ja) | 2018-04-18 | 2020-07-22 | ダイキン工業株式会社 | R32、R125、R143a、R1234yf及びR134aを含む冷媒を含有する組成物、並びに、その組成物を用いた冷凍方法、冷凍機の運転方法及び冷凍機 |
CN110903811B (zh) * | 2019-11-14 | 2021-07-13 | 浙江巨化新材料研究院有限公司 | 一种直接取代r-22的制冷混合工质 |
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- 2003-09-19 FR FR0311025A patent/FR2860001B1/fr not_active Expired - Lifetime
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- 2004-09-02 WO PCT/FR2004/002231 patent/WO2005028586A2/fr active Application Filing
- 2004-09-02 JP JP2006526657A patent/JP4855256B2/ja not_active Expired - Fee Related
- 2004-09-02 EP EP04787286A patent/EP1664234B1/fr not_active Expired - Lifetime
- 2004-09-02 ES ES04787286T patent/ES2336795T3/es not_active Expired - Lifetime
- 2004-09-02 US US10/570,938 patent/US7504043B2/en active Active
- 2004-09-02 EP EP08171320A patent/EP2031033A3/fr not_active Withdrawn
- 2004-09-02 DE DE602004024548T patent/DE602004024548D1/de not_active Expired - Lifetime
- 2004-09-02 AT AT04787286T patent/ATE451437T1/de not_active IP Right Cessation
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10035939B2 (en) * | 2016-09-27 | 2018-07-31 | Icool Ningbo Co.,Ltd | Refrigerant composition and its preparation method |
Also Published As
Publication number | Publication date |
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WO2005028586A3 (fr) | 2005-06-30 |
CN1852963B (zh) | 2010-12-15 |
US20070187638A1 (en) | 2007-08-16 |
ATE451437T1 (de) | 2009-12-15 |
DE602004024548D1 (de) | 2010-01-21 |
CN1852963A (zh) | 2006-10-25 |
JP2007505963A (ja) | 2007-03-15 |
FR2860001B1 (fr) | 2008-02-15 |
EP1664234A2 (fr) | 2006-06-07 |
JP4855256B2 (ja) | 2012-01-18 |
WO2005028586A2 (fr) | 2005-03-31 |
EP1664234B1 (fr) | 2009-12-09 |
EP2031033A2 (fr) | 2009-03-04 |
ES2336795T3 (es) | 2010-04-16 |
EP2031033A3 (fr) | 2012-05-16 |
FR2860001A1 (fr) | 2005-03-25 |
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